


I'll gain your trust

by fromacloset



Category: Supernatural
Genre: Age Play, CG/L, Caretaker Sam, Caring Sam Winchester, Cuddling & Snuggling, Dom/sub, F/M, Fluff and Smut, Little Reader, Little Space, Non-Sexual Age Play, Non-Sexual Intimacy, Praise Kink, Protective Sam Winchester, Spanking, i'll add more later, mentions of past sexual abuse
Language: English
Status: Completed
Published: 2019-10-25
Updated: 2019-11-05
Packaged: 2021-01-03 03:27:06
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 3,820
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21172652
Author URL: https://archiveofourown.org/users/fromacloset/pseuds/fromacloset
Summary: Sam had fallen for the waitress at the diner. Slowly Sam and the reader form a relationship and with her past, Sam wants to take things slowly to care for her the way she wants and needs





	1. From the start

**Author's Note:**

> I know it's been a long time since I've posted. It's taken me a long to, it has been a very rough year. The back story is mine so this is personal.
> 
> Hope you like this

When you first met Sam it was when he was on a hunt. You were a waitress at the diner and while you blushed at both Winchester brothers, Sam was the one who caught your attention and you caught his. The diner was in Lebanon, Kansas and you have seem them around town, but you were happy when your shifts changed so you could see more of him.

Slowly you learned of the things out there, what Sam and Dean really did. You heard what the kids were saying on the street, but you brushed it off. Sam was scared that you would want nothing to do with them, but this only made you want to be with them more. 

Over the next couple of months, you started to open up to Sam. No one knew what it was like to burry things down like Dean Winchester. Sam too, but Dean was the one that suggested to Sam that there was more than you led on. But like you always do, you smiled and reassured Sam that everything was okay. 

3 months into dating, you told Sam talked about taking things a little kinkier in the bedroom and Sam was all too happy to oblige. You knew that there was something very domesque of him and you were a bit of submissive.

Sam wanted to take it slow with you though. The one thing you had shared with Sam was that you had been sexually assaulted earlier in the year. Sam wanted to be as gentle and slow as possible with you, but not treating you like someone who would break. So, you two started small when getting kinky.

“Are you sure?” Sam asked. You smiled and nodded.

“I am. Promise.” He leaned down and kissed you softly, you smiled against his lips and he gave you a small back.

“Elbows and knees, ass in the air.”

Wearing only his t-shirt and underwear, you did as Sam told you. A light swat came to your left butt cheek. You lightly giggled and Sam smiled as he gave you another swat. You pushed your ass to the air and a hard spank came to your left butt cheek. You inhaled.

“Thank you.” you said.

“Mmmm, so polite” Sam lightly teased and you looked back, smiling. He smiled as he spanked you harder, this time landing near your pussy.

“Hnn, thank you.” you whined.

“Good girl” he praised and your stomach fluttered, soaking your underwear. Sam rubbed a hand over your soaked panties “So wet”

“Yeah.” You whimpered. Sam gave sharp spanks to your pussy and you moaned, pressing down.

“Oooh, you want more, don’t you.” you blushed and nodded.

Sam kept giving little spanks to your pussy before moving back to your ass and pulled down your panties. He lightly touched our entrance and you gasped. You gasped again when a sharp spank came to your right buttcheek. Sam massaged your butt and sat down, pulling you onto his lap, holding you close and kissing your temple.

“What a good girl you were for me” Sam whispered, leaning his forehead against your shoulder, kissing your back. He cradled your head to his chest. “I’m proud of you”

“Thank you, for spanking me.” you whispered, nuzzling closer to him.

“You’re welcome, baby” he kissed your temple again. 

“I’m all wet” you blushed hiding against his neck and Sam lightly chuckled. 

“I know you are. How about I clean you up, huh?”

“Kay” your voice a bit small and Sam hugged you closer.

“I love you so much, sweetheart” you hugged Sam tight.

“I love you”

Sam placed you on the bed and you spread your legs, Sam smiled leaning down and kissing your forehead. He went to the bathroom and grabbed a warm wash cloth and came back. You jumped a little when the warm cloth, touched your wet center and you relaxed as Sam wiped you.

“There we go, baby. Can I hold you tight and give you snuggles?” you nodded, blushing.

You had mentioned to Sam that sometimes you liked to be taken care of, that you resorted to little tendencies. Sam was happy to take care of you; he wanted to make you feel as comfortable as possible. 

Sam put the cloth down and got on the bed, sitting you on his lap, pulling a blanket over you. In a way he cradled you, laying back and holding you tight against his chest. You rested your head against his shoulder and nuzzled against him. 

It’s been a year now that you and Sam have been dating and you started to get kinkier. One night you asked Sam if you could call Sam daddy during sex, if he could refer to himself as daddy. Your legs were spread and Sam was rubbing your clit, he watched as you moaned and arched our back.

“Daddy” you moaned, clinging to the sheets.

“You like when daddy does that?”

You froze. You were triggered for some reason, even though it had been a year. As soon as you froze Sam was by your head, one hand holding yours and the other stroking your hair. 

“I’m right here.” He whispered.

“I’m sorry” you started to cry.

“You have nothing to be sorry for” 

“I’m sorry.”

“No, sweetheart, I’m sorry. I triggered you.” You covered your face with your free hand crying harder. “What do you need? Can I hold you?” you nodded.

Sam scooped you up in his arms like you were a small child. Your legs wrapping around his waist, he cradled your head to him. Sam gently swayed side to side, letting you cry. He encouraged you to let you cry, that you were safe and he had you. 

A few minutes later, your tears subsided and Sam held you tight, kissing your temple. You clung to him tighter, not wanting to let him go. 

“Can you look at me?” he asked sweetly and you lifted your head to look at him. Sam smiled softly and rubbed his nose with yours. You blushed, cracking a small smile. “Hi, beautiful” he whispered. “Can I get you dressed? Then get you a snack?” you nodded.

“I wear one of your shirts?” you whispered. Sam nodded, wiping some tears on your cheeks.

“Yeah. I am so proud of you.”

“Yeah?” 

“Yeah, you make me so proud”

Sam sat you on the bed and grabbed the baby wipes, you spread your legs and he opened the package, wiping you. The coolness made you gasp a bit and then you covered your face, giggling a bit. Sam opened a drawer and held up a pullup or underwear. 

“Which one, sweet girl?” he cooed a bit. You peaked from your fingers and then hid your face.

You and Sam had embraced your little side more. It was more of having someone to make sure you ate, reminded you to have water, someone to tell how your day was. And take care of you in a non-sexual physical way. 

Sam wanted you to let him know what you needed to make you feel small and safe. When you really wanted to be little and regress, you confessed that pullups is what you liked. He never forced anything on you. He always gave you a choice about pullups or underwear to determine the care you wanted and needed.

You pointed to the pullup and Sam nodded, grabbing the lotion and powder. You never used the pullups, it wasn’t about that at all. 

Sam rubbed the lotion on you and lightly powdered the pullup, slipping it over you bottom, He fixed it and then sat you up. He grabbed a t-shirt and put it on you. He lifted you up in his arms, rubbing your covered bottom.

“There we go. All nice and snuggly.” Sam kissed your nose. “Let’s get you some snacks and snuggles”


	2. Tell all

**Notes for the Chapter:**

> A bit short.
> 
> This is what happened to me, her backstories about the caregivers.

Sam was in the library doing research and you walked in, rubbing a hand on his back. He looked up and smiled at you, opening his arms and you sat on his lap.

“Sam, can we talk?” you asked.

“Of course.” He was concerned.

“I just wanted to explain about the other day. When I froze. Just let me get it out.” Sam nodded, not wanting to interrupt. “I told you about being assaulted, but there was a bit more. I was speaking to someone for five months, he became a caregiver for me and my little. I respectively ended things when it happened and explained everything and he never responded to me. He promised he wouldn’t go anywhere and I even asked what if I push him away and he said he was going to stay right here but he didn’t. I get it, I ended things, but no response doesn’t seem fair.”

“It’s not” Sam said, holding you tighter.

“Then a few months later I met someone else online and we were just talking, but it turned into a caregiver situation. I told him everything about the older caregiver and he of course said he was going to be there. A few months later I felt us drifting apart I asked if he still wanted to be a caregiver, that it was okay if he wanted to stop that relationship, but he kept saying it was okay. Then he ended it suddenly, which confused me, because I kept making sure if he was sure.” 

You rested your head on his shoulder and he wrapped his arms around your waist. You two sat there in silence for a bit. Sam wanted to let it sink in and just wanted to hold you. 

“So, that’s why I was really closed off when we first met and why even though we’ve been dating for a year, I’m still a bit closed off. I thought I was ready to take things a little further, trying out daddy kink, but it just-it reminded me of the old caregivers.” After a moment Sam spoke

“Thank you so much for telling me all that. That’s really brave, I know it wasn’t easy. I am really proud of you” he spoke quietly. “I want to take things as slow as possible. I want to give you everything you need and want. You are in charge.”

“You’re the dom” you whispered

“And as a dom I need to do what’s best for my sub. Right now, what’s best is to have you call the shots. I will give you options and move forth from there. Like when I gave you the options underwear or pullups, to gage what kind of care you wanted and needed. Once you picked pullups I knew that then I could step in and be in charge. However anytime you want to stop anything, you just tell me.” You nodded.

“You’ve been really good to me and for me, Sam.” you whispered.

“I want you to trust me and hearing what has happened to you with the past caregivers; it makes me sad and upset because no one deserves that. You don’t deserve that. Can you straddle my lap for a moment?” You did as he said and he cupped your cheeks. “Please take as much time as you need to heal. Take as much time as you need to really trust me. What you’ve been through is a lot, especially to go through it alone and we’ve been dating for a year, and I know that you think that you should be over everything. Everyone is different. It takes time. You’ve got time. It sounds like they’ve made promises and then broke them.” You nodded “So I’m not going to do that, because that’s not fair to you. But know that I want what’s best for you and if you need or want anything, please ask me, I want to give you the safety you deserve. Okay?”

You wrapped your arms around his neck, pressing yourself close to him. Sam wrapped his arm around your waist and back of your neck. You two stayed like that, you hadn’t realized you fell asleep. You felt Sam lift you up and you stirred, wrapping your legs around his waist.

“I just want to stand and hold you, baby. Keep napping” he whispered. You nuzzled against his neck and drifted back to sleep. 

Sam watched you carefully throughout the next couple of weeks, he could tell that you seemed not distant, but there was something on your mind. He came up behind you and rubbed a hand on your back.

“Y/n/n?” he asked and you looked up at him. “Is there something on your mind?” your back stiffened and Sam removed his hand. 

“Sorry, is it obvious?” you brought your knees to your chest on the chair.

“It’s not obvious, I’ve just been keeping a closer watch on you since our big talk.”

“I want to talk to you about it, but I didn’t know how to approach it.”

“That’s okay. When you’re ready, I will listen.”

“I’ve just-I’ve thought about reaching out to my first caregiver. I know I shouldn’t, but I feel like I can’t move forward without hearing from him.”

“You need the closure.” Sam confirmed and you nodded. “Okay. How can I help, if you want my help.”

“I guess, what do I say? If it’s a right decision”

“That’s all up to you. If you would like me to help you word things, I can. “

“I do want to reach out. I think I need to.”

“Okay.”

“Thanks, Sam.”

“You’re welcome”

The next couple of days you debated what to say. How it would affect Sam.

**Notes for the Chapter:**

> I'm debating about reaching out to him. I don't know.


	3. Take your mind off things

You sat down and wrote a messaged your old caregiver, and now you wait for his response, if he does respond. He’s known not to. That didn’t matter, you took the leap and you still felt unhappy. You felt like there was a whole in your chest. You felt light. You felt empty.

Nothing Sam or Dean said could change it. You smiled and laughed when you thought things were funny and you came across like your normal self to anyone who didn’t know you, but Sam and Dean grew worried.

“I don’t know, Dean.” Sam said

“Has she gotten better?” Dean asked grabbing a beer.

“Sort of. She’s her usual self at work. She likes working there, but at home…”

“I know that what she told you is confidential and you two have a special relationship, you told me some things, but I’m also worried. I know about the assault, but not about what happened. She just said that she got hurt, emotionally”

Dean knew Sam was a dom, he had those traits, Dean ahd his kinks, so he would never judge. He knew that you and Sam had a different type of relationship when it came to dom/sub. He’s seen Sam care for you like a child and even walked by and heard Sam talk to you like you were little. Dean just shrugged, if that’s what you need, power to you.

Sam got nervous seeing how almost scared Dean was. He had hoped that his older brother would give him some reassurance or something. Dean hated to see his brother like this and wanted to fix it.

At work you smiled and served the tables, you loved your job, but even your coworkers noticed that there was something off with you. 

“Hey, Y/n, are you okay?” your co-worker Janice asked 

“Yeah, why?” you turned, smiling a bit.

“Just, you seem different is all.”

“Oh. I’m okay. Thank you.”

You got home after work and went to your room and got changed into your pajama shorts and comfy shirt. You opened the door and saw Dean there.

“Oh, hey. You said.

“Hey. I was about to make some coffee, did you want?” he asked.

Yeah, sure. Where’s Sam?”

“He’s in the library, I’ll bring your coffee there” Dean said.

“Okay” you smiled and walked to the library.

Sam turned when he saw someone come in and smiled seeing you. He pushed his chair back and you climbed on to his lap. Sam held you close, combing his fingers through your hair. Your head rested on his shoulder and you yawned.

“You tired” he smiled softly.

“Mm. Dean is bringing me coffee.”

“Good. How was work?”

“It was good. Made good tips. I like the morning shift.”

“I’m glad. I’m proud of you, baby.”

“Thanks.”

You and Sam wondered what was taking Dean so long. You started laughing when Dean walked in with milk foam on your coffee. You sat up a bit, smiling.

“I thought I would foam the milk, like the latte you like. I know that this is coffee with milk and not espresso and milk, but yeah.” Dean said proud of himself.

“Thank you, Dean. That is very nice you”

“Huh” Sam said impressed seeing the foam.

“What?” Dean asked.

“Nothing, that’s just really good” 

“Yeah, seriously. This is great Dean.” You smiled taking a sip.

“Good I’m glad.”

“Have you eaten anything?” Sam asked, rubbing circles on your back and you shook your head sipping the coffee.

“How about some bagel bites. We stocked up.” Dean suggested and you smiled nodding .

“I’ll go put them on.”

Dean walked away and you placed the coffee down, chuckling a bit and curling into Sam. He held you tight.

“Can I do something for you?” Sam asked. You blushed and nodded. “I know that blush, that’s not a little blush, my girl wants to be a bit rough.”  
“Yeah” you said.

“Okay. Well, have your coffee, bagel bites and rest a bit and then I’ll get you ready for bed.”

“Oh, but-“ Sam smiled.

“I mean, I’ll get you tired before you take a nap” Sam winked. The brothers knew not to disturb you after you’ve had a morning shift.

You relaxed into Sam and he combed his fingers through your hair and you lightly spread your legs. Sam kissed your forehead and reached down rubbing a finger against your underwear feeling how wet you were.

“Mmm” you moaned.

“So wet for me.”

“Mmmhmm. I’ve been charging my toy”

“Good girl.” He lightly growled in your ear, tugging you hair a bit. You opened your mouth as you felt his finger slip past your underwear.

Sam knew that sometimes you needed to take your mind off of things and he was happy to help. Though he toyed with you while you waited for Dean, he was always made sure to watch you close to gage how you were doing.


	4. Chapter 4

You messaged your old caregiver and he didn’t respond once again. You were so stupid for thinking that he would. You walked to the kitchen and saw Sam sitting at the table. You walked over and straddled is lap, facing him. You curled bit, bringing the sleeve of your sweater to your mouth. Sam rubbed a hand on your back.

“Baby?” he asked quietly.

“Can I have the care like I’m in a pullup, but not be in one?” you asked

“Sure.” He said pulling you tighter to him. “Just be my baby, but no pullup. I mean, you’re always my baby, but you know” 

“Yeah.”

“Okay, sweet girl. Is there something you want to talk about?”

“I messaged my caregiver. No response like before.” Sam rubbed a hand over your bum, knowing that calmed you and made you feel small. “And I feel bad because I hurt you.” Sam’s brow furrowed.

“Is that what you think, baby? That you hurt me?” you nodded, starting to cry a bit. Sam moved you so he had you sort of cradled, wiping some tears. “You did not hurt me one bit. You needed some closure. I am so proud of you, honey.” You looked at him wide eyed.

“You are?” Sam smiled softly, nodding and kissed your nose. You smiled a bit.

“You were so brave reaching out and that is something I am proud of you for. It takes lots of courage.” 

“Thank you.” you looked down.

“Thank you for telling me. Now, I know you said no pullup, but, how about your onesie?”

“The raglan one?” 

“Okay, sweetie. If you want” you nodded.

Sam lifted you up in his arms, carrying you like a child and brought you to the bedroom. He sat you down on the bed and pulled off your sweater and you blushed when he saw that you weren’t wearing a bra. He grabbed your onesie and helped you into it. He laid you down, kissing your forehead and lifted your legs up.

“I’m going to wipe you and put cream and powder to make you feel small and then put fresh undies on.” Sam explained and you smiled. He grabbed your baby blanket, handing it to you. 

Sam pulled your underwear off and grabbed the wipes. You shivered at the coolness and then jumped when you felt him rub the cream into you. Sam wiped his hands with the wipes and squirted more cream, massaging it into your legs.

You giggled hiding behind you blanky. He massaged your foot, and you relaxed more as he massaged your other leg. When he was done he grabbed the baby power and lightly sprinkled it on you and grabbed fresh underwear and placed them on you. He snapped the onesie up and lifted you back in his arms, lightly rubbing your bum. 

“You’re my good girl, do you know that?” you nuzzled into the side of his neck, clutching your blanky. You’re my good girl and I love you so much.” You giggled, regressing more and more. Sam nibbled at your cheek. “Now, what do you need? Some food?” Sam rubbed your stomach and you nodded. “Yeah, let’s make some food for you.

Sam brought you into the kitchen and placed you on the table and kissed your forehead. He walked over to the oven and turned it on. He went to the freezer and grabbed chicken nuggets, macaroni and cheese and onion rings. 

He placed them all on the tray and waited for the oven to be ready. He placed the food in and set the timer, lifting you in his arms. Sam led you until the timer went off. He grabbed your plate and he pulled the stuff out of the oven.

“This smells so good, doesn’t?” he cooed and you nodded, smiling big.

Sam pulled your chair closer to the table and placed a towel on the table, he went and scooped onion rings onto your plate, some chicken nuggets and mac and cheese. He did the same thing for him and brought both plates over. He kissed the top of your head and grabbed some juice for you.

Sam sat at the table and scooped mac and cheese onto a spoon and blew on it, place it down, wrapped a towel around your neck and fed you the food.

**Author's Note:**

> Comment and kudos


End file.
